Reader Still "Single" writes,

I've been with my partner for over 5 years, the last 3 living together. He had been married before and had a divorce they make Lifetime movies about, and at the end of it, he had full custody of his kids and was $100k in debt. When we began dating (about 5 years after his divorce), he was very clear from the beginning that marriage really wasn't on the table. He didn't believe in it and had too many scars.

He's done a lot of therapy over the years and is also on meds for anxiety. We had a rocky start, mostly due to leftover stuff he carried into our relationship, but we learned how to dodge landmines and he learned how to shift his thinking. All good things. We've been pretty close and happy for most of our time together, particularly these last couple years. And I always knew that if it was on the table, I'd marry him in heartbeat and he knew that.

So when I was faced with medical issues and potentially astronomical medical bills (I have terrible insurance, he has a Cadillac plan), he said he could get behind the idea of marrying for financial reasons if it would benefit both of us (and specifically, have a neutral-to-positive impact on him). And I thought, "Yay! It's a win-win situation!" So we talked it through, ran some numbers, and the next thing you know we've got a wedding planned for a month out (medical reasons being the impetus for haste).

Then, two days before the wedding, someone mentioned 'marriage tax penalty' to Tom. He immediately went into research mode and no matter how you sliced it, because we both make over 6-figures, it was going to impact him financially to some degree. But it was two days before our wedding and we decide to have it and it was lovely.

Now it's a week since then and our signed marriage license is laying on the table between us, unregistered and unofficial. If we file the license, I'm happy and he's unhappy. If we don't file it, I'm unhappy and he's happy. We're in a no-win, damned-if-you-do-damned-if-you-don't situation. I honestly don't know how to resolve it and I'm wishing like hell we'd never even gone down this path. Please tell me there is another path.

Dear SS,

First I was thinking, this guy sounds like a jerk. Then I went back and read it again. For a thought experiment, I switched it in my head like this:

I'm a single mom who got financially destroyed in a divorce. It destroyed my mental health as well, to be honest, and I've struggled with anxiety since then. I have sole custody of my kids and they are my life. I'm now living with my boyfriend of five years, who has always known I no longer (if I ever did) believe in marriage and refuse to in any way compromise myself financially again. We are both doing pretty well at our jobs now, although I am still massively in debt from the divorce. He has a medical condition and asked me to marry him in order to get on my better insurance plan, although he has also always been more into the marriage idea than I was anyway, to be fair. I agreed in order to give him the better health care, but then a friend told me that I will be losing quite a bit of money in taxes if I get married. We had the wedding and it was really nice, but I just cannot bring myself to file the paperwork. Not only do I not believe in marriage, but I feel that I am putting myself in financial jeopardy again since I am struggling to repay debt and pay for the kids' needs (and college one day) all on my own. What should I do?

If we switch the genders, which then kind of nullifies any societal idea that as the man he "should" be rescuing you from this potentially difficult financial situation, it seems obvious to me that most people would tell this woman to stick to her guns and let the guy figure out his own bills. And your partner probably would have done the same if he didn't think it would devastate you and seem callous in the face of your medical issues.

Your partner was honest from the get-go about his lack of desire to remarry, which already makes him a great guy compared to all the liars out there. He has a lot on his plate as a solo parent, and probably never should have agreed to marry you. But he did, in order to be a stand up guy, and because he loves you. Then he couldn't back out of it because then he would have been The Jerk Who Made You Cancel Your Wedding, like Mr. Big in the Sex and the City movie. So he married you, but now he just can't bring himself to screw himself and his kids out of another few thousand dollars a year, or more, and thus your papers sit waiting for one of his kids to spill something on them or throw them out by mistake.

I don't think this stuff makes him a bad person. It doesn't make him a bad partner. He is what he is. He lives with you and therefore I assume he will care for you physically in whatever way he can. But don't make him file the paperwork. Consider the wedding a commitment ceremony. It was a beautiful day and I'm sure you had lots of fun and were surrounded by loved ones and happiness. That can be the win-win, you got a wedding and to live with the guy you love after it, and he gets to not compromise his philosophy on marriage or his finances and to stay true to himself. The only "lose" part is the medical bills and I am betting if they would put you in the poorhouse, your live-in boyfriend of 5 years who consented to have a wedding with you would help you out with them. Relatedly, I had to research this marriage penalty thing and it seems like a positive side here is you guys seem to make a lot of money, or else you'd actually have a marriage bonus. I assume this is also impacting your partner's viewpoint. If he thought these bills would destroy you, I think he would have filed the papers.

Remember, it still stands that you were cool not getting married till you needed insurance, and even if your medical issues have given you an epiphany that you can't live without marriage (but this doesn't seem to be the case), it didn't give him the same epiphany, nor is it fair to think it would. If you'd like to be with a more romantic guy who would marry you quicker, you need to meet a guy who isn't battle-scarred from divorce and who isn't a single parent. But in that scenario, it is you who would now be the jaded (kind-of-) divorcee, ironically.

Good luck and let me know if you end up the Mrs. or not. And till we meet again, I remain, The Blogapist Who Says, Also Read So Much For That by Lionel Shriver, You'll Appreciate It.

This post was originally published here on Dr. Psych Mom. Follow Dr. Rodman on Dr. Psych Mom, Facebook, Instagram, Twitter, and Pinterest. Order her book, How to Talk to Your Kids about Your Divorce: Healthy, Effective Communication Techniques for Your Changing Family. This blog is not intended as diagnosis, assessment, or treatment, and should not replace consultation with your medical provider.